Pleasant Prairie is a village in the U.S. state of Wisconsin. Located in Kenosha County along the southwestern shoreline of Lake Michigan, Pleasant Prairie was home to 21,250 people at the 2020 census. The village is positioned directly south of the city of Kenosha and directly north of the Illinois border. Although located just 37 miles south of Milwaukee, it is part of the U.S. Census Bureau's Chicago combined statistical area and metropolitan statistical area despite being 57 miles north of Chicago.